DMC, the original. Fighting Griffon and him using his hard to avoid "energy bars" attack...
And the goddamned camera switches to a 2D perspective, putting your survival chances from "low, but if you're good you'll make it" to "pure luck. you're fucked, baby"
Half of the last boss's attacks fit too, since it's basically 100% luck if you're gonna die a horrible death or avoid it completely (there's rarely an in-between).
System Shock 2, no specific pre-made moments but ones made by yourself. (You're low on ammo on your soon useless handgun, and the goddamned Many gloats and explains how you only have your hatred and individuality left, and you haven't even SEEN their most beautiful creation yet. That felt unfair. It wouldn't be so bad if my ammo WASN'T running low and my weapons WEREN'T failing me, damnit!)
My wife adds that to her, it was Aeris dying because she had spent a lot of time making Aeris her best party member because she honestly liked the little flower girl, just to have all of it ruined in an instant. (Me, I didn't care much for Aeris, wimpy attacks equals no party slot IMO)